Chelsea F*cking Handler

Let's Be Honest with Kristin Cavallari

Dear Media

Relationships, Society & Culture

4.2 • 3.3K Ratings

🗓️ 26 May 2026

⏱️ 49 minutes

🔗️ Recording | iTunes | RSS

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Summary

This week, I sit down with the one and only Chelsea Handler! And in true Chelsea fashion, nothing is off limits. We get into how she's staying single, getting hotter & giving less f*cks than ever. We dig into why she has zero interest in long-term relationships, the one thing therapy changed about her, and why her 50s are the best years yet. She also opens up about Hollywood, confidence, sex, if sobriety is a dealbreaker, and the freedom that comes with truly knowing yourself. We also talk about her dating life, celebrity disasters, why she loves being alone, and the biggest lessons she’s learned getting older. Chelsea is the best, and I think you guys are going to love this conversation!

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Transcript

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0:00.0	The following podcast is a Dear Media production.
0:04.4	This is Let's Be Honest with Kristen Cavalery, a podcast all about getting real and open on everything from sex, relationships, reality TV, wellness, family, and so much more.
0:15.5	And just a fair warning, there will probably be some oversharing.
0:22.4	Chelsea, I'm so excited that you're here.
0:24.9	How the hell are you? It's so good to see you. It's good to see you too.
0:28.6	I'm good. I'm good. I just missed you in Nashville. I'm so bummed.
0:32.4	I know. I had fun with our other, with our gaze. I only had one of the gays, Justin, because
0:36.8	the other one is impaired. Just got his cast off. now he's in a boot for the rest of the month okay for a baby just in time for summer though it'll be he'll be healed in time for summer thank god yeah so you're in the middle of your tour high and mighty tour i'm on the road everybody chelseahandler dot com that's where you get your ticket and you've been on the road since february february and i'll go through December, yeah. Through just, oh, so you've added.com. That's where you get your ticket. And you've been on the road since February?
0:55.9	February and I'll go through December. Yeah. Oh, so you've added. You've been adding dates? We added a second half. We do a first leg and then a second leg. So my second leg is about to begin. How the hell? I will never understand how you guys do it. How do you survive? Because I did a podcast store that was a week and I about died on that. Yeah, it's you have to be very what's it's a resilient.
1:14.5	Yeah. And do it. How do you survive? Because I did a podcast tour that was a week and I about died on that.
1:11.1	Yeah, you have to be very what's, it's resilient. Yeah. And you also, I've been doing it for so long that I know the drill like about sleeping and that I have to have sleep. Yeah. Like, and where I sleep, like I won't sleep in a city that doesn't have the kind of hotel that I need to have. otherwise we fly out to a city that does.
1:30.0	Oh, smart.
1:30.6	And we just, like, use our time more efficiently, I think. But I'm in the rhythm, like, that's my lifestyle, because I've been doing stand-up for so many years, touring for so many years that, like, I'm comfortable in hotels. Like that's where I vibe. I have my gym. I have room service. I don't have to fuck with anybody if I don't want to fuck with anybody.
1:47.6	So I kind of like... Like I'm comfortable in hotels. Like that's where I vibe. I have my gym. I have room service.
1:44.7	I don't have to fuck with anybody if I don't want to fuck with anybody. So I kind of like that like sometimes I come home and I'm like, you know, my house has to be like has been turned into a hotel just because it's more comfortable. I'm like, hello, can I get some room service? I feel like eating a bed, you know? Yeah. I do feel like eating a bed. I have to be honest. I always fucking eat a bed.
2:02.4	No, it's nice. I get it. There's something to it.
2:04.5	Yeah. service I feel like eating a bed you know yeah I do feel like eating a bed I have to be
2:00.9	honest I always fucking eat a bed no it's nice I get it there's something to it yeah well
2:05.3	and then I just watched the Kevin Hart roast yes I mean you are a busy woman so you're
2:09.6	on tour then you fly out was it out here that they you guys yeah for the roast one thing I did
2:14.1	notice though was how fucking incredible you looked I mean honestly like the best you, the best you've ever looked. Thank you. Truly, I was like, damn, Chelsea. And then you posted a few videos and photos, too. And I was like, girl, you're doing it. So you turned 50, not that long ago. Yes. Well, yeah, I'm 51 now, I believe. So, I mean, it keeps happening. Age keeps going. I like, I like the number 50. It had a nice round number and it was a big deal. I was like, let me just ride this out.
2:38.0	And then it was like, I like the number of 50. It had a nice round number and it was a big deal. I was like, let me just ride this out. I think you can. I think it wrote itself out. Now I'm 51. That's right. We can still say recently turned 50. I think it still applies. But so I want to know what nips and tucks are we doing? What are you doing to stay looking so good? Because you do. You look great.
	...

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